Phones Texts Are Not Working

So my friend has two different phones one is an android the other is an apple. Up until now my phone had been working perfectly fine but I have it set to where both the numbers are in one contact. You can switch between them at ease on which phone I need to text. Well the last time I tried to switch back to the android number from the iphone number it just kept on trying to send the imessage to the iphone? I eventually got it to text the android number but not my phone is being very buggy. I have him pinned and whenever he sends me a text it sends me it through the pinned contact and from the same number on my regular message area. Also when I get a text instead of saying my contact name it says his number. I have tried deleting he contact and re making it. I even made the iphone number its own contact and it still does not work. I am still having these problems and I’m honestly getting so mad and it’s annoying. I don’t know how to fix it. Please Help!